From e38f5a4db7d41eb2a5cb9e62912b07b4da7c0419 Mon Sep 17 00:00:00 2001
From: Jason Carreira <jcarreira@gmail.com>
Date: Wed, 11 Mar 2026 18:18:02 -0400
Subject: [PATCH] fix(session): auto-clear stuck conversation on invalid tool
 call ID mismatch (#555)

Co-authored-by: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 src/core/errors.ts          | 10 ++++++++++
 src/core/session-manager.ts | 23 ++++++++++++++++++++++-
 src/tools/letta-api.ts      |  3 ++-
 3 files changed, 34 insertions(+), 2 deletions(-)

diff --git a/src/core/errors.ts b/src/core/errors.ts
index 1cfa88a..477a90a 100644
--- a/src/core/errors.ts
+++ b/src/core/errors.ts
@@ -59,6 +59,16 @@ export function isAgentMissingFromInitError(error: unknown): boolean {
   return agentMissingPatterns.some((pattern) => pattern.test(msg));
 }
 
+/**
+ * Detect if a recovery details string indicates mismatched tool call IDs.
+ * When this happens, the conversation is permanently stuck -- the pending
+ * approval can never be resolved because the server expects different IDs.
+ * The conversation must be cleared and recreated.
+ */
+export function isInvalidToolCallIdsError(details: string): boolean {
+  return details.toLowerCase().includes('invalid tool call id');
+}
+
 /**
  * Map a structured API error into a clear, user-facing message.
  * The `error` object comes from the SDK's new SDKErrorMessage type.
diff --git a/src/core/session-manager.ts b/src/core/session-manager.ts
index 70a3792..cd038a6 100644
--- a/src/core/session-manager.ts
+++ b/src/core/session-manager.ts
@@ -8,7 +8,7 @@
 
 import { createAgent, createSession, resumeSession, type Session, type SendMessage, type CanUseToolCallback } from '@letta-ai/letta-code-sdk';
 import type { BotConfig, StreamMsg } from './types.js';
-import { isApprovalConflictError, isConversationMissingError, isAgentMissingFromInitError } from './errors.js';
+import { isApprovalConflictError, isConversationMissingError, isAgentMissingFromInitError, isInvalidToolCallIdsError } from './errors.js';
 import { Store } from './store.js';
 import { updateAgentName, recoverOrphanedConversationApproval, isRecoverableConversationId, recoverPendingApprovalsForAgent } from '../tools/letta-api.js';
 import { installSkillsToAgent, prependSkillDirsToPath } from '../skills/loader.js';
@@ -399,6 +399,16 @@ export class SessionManager {
             } else {
               log.warn(`Proactive approval recovery did not find resolvable approvals: ${result.details}`);
             }
+            // Even on partial recovery, if any denial failed with mismatched IDs the
+            // conversation may still be stuck. Clear it so the retry creates a fresh one.
+            if (isInvalidToolCallIdsError(result.details)) {
+              log.warn(`Clearing stuck conversation (key=${key}) due to invalid tool call IDs mismatch`);
+              if (key !== 'shared') {
+                this.store.clearConversation(key);
+              } else {
+                this.store.conversationId = null;
+              }
+            }
             return this._createSessionForKey(key, true, generation);
           }
         }
@@ -585,6 +595,17 @@ export class SessionManager {
         const result = isRecoverableConversationId(convId)
           ? await recoverOrphanedConversationApproval(this.store.agentId, convId)
           : await recoverPendingApprovalsForAgent(this.store.agentId);
+        // Even on partial recovery, if any denial failed with mismatched IDs the
+        // conversation may still be stuck. Clear it so the retry creates a fresh one.
+        if (isInvalidToolCallIdsError(result.details)) {
+          log.warn(`Clearing stuck conversation (key=${convKey}) due to invalid tool call IDs mismatch, retrying with fresh conversation`);
+          if (convKey !== 'shared') {
+            this.store.clearConversation(convKey);
+          } else {
+            this.store.conversationId = null;
+          }
+          return this.runSession(message, { retried: true, canUseTool, convKey });
+        }
         if (result.recovered) {
           log.info(`Recovery succeeded (${result.details}), retrying...`);
           return this.runSession(message, { retried: true, canUseTool, convKey });
diff --git a/src/tools/letta-api.ts b/src/tools/letta-api.ts
index 5e393cc..8a872af 100644
--- a/src/tools/letta-api.ts
+++ b/src/tools/letta-api.ts
@@ -895,8 +895,9 @@ export async function recoverOrphanedConversationApproval(
               streaming: false,
             });
           } catch (batchError) {
+            const batchErrMsg = batchError instanceof Error ? batchError.message : String(batchError);
             log.warn(`Failed to submit approval denial batch for run ${runId} (${approvals.length} tool call(s)):`, batchError);
-            details.push(`Failed to deny ${approvals.length} approval(s) from run ${runId}`);
+            details.push(`Failed to deny ${approvals.length} approval(s) from run ${runId}: ${batchErrMsg}`);
             continue;
           }